CA2427812A1 - Novel .beta.-lactam compounds and process for producing the same - Google Patents
Novel .beta.-lactam compounds and process for producing the same Download PDFInfo
- Publication number
- CA2427812A1 CA2427812A1 CA002427812A CA2427812A CA2427812A1 CA 2427812 A1 CA2427812 A1 CA 2427812A1 CA 002427812 A CA002427812 A CA 002427812A CA 2427812 A CA2427812 A CA 2427812A CA 2427812 A1 CA2427812 A1 CA 2427812A1
- Authority
- CA
- Canada
- Prior art keywords
- lower alkyl
- hydrogen
- beta
- alkyl
- novel
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 125000000217 alkyl group Chemical group 0.000 abstract 6
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 150000002431 hydrogen Chemical group 0.000 abstract 3
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- 125000003341 7 membered heterocyclic group Chemical group 0.000 abstract 1
- 241000192125 Firmicutes Species 0.000 abstract 1
- 206010041925 Staphylococcal infections Diseases 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 208000015688 methicillin-resistant staphylococcus aureus infectious disease Diseases 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D477/00—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring
- C07D477/10—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
- C07D477/12—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2 with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 6
- C07D477/16—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2 with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 6 with hetero atoms or carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 3
- C07D477/20—Sulfur atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D477/00—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring
- C07D477/02—Preparation
- C07D477/06—Preparation from compounds already containing the ring or condensed ring systems, e.g. by dehydrogenation of the ring, by introduction, elimination or modification of substituents
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Molecular Biology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
- Cephalosporin Compounds (AREA)
Abstract
The present invention is directed to a .beta.-lactam compound of the formula [1];
(see formula 1) wherein R1 is a lower alkyl, a lower alkyl substituted by a hydroxy; R2 is a hydrogen, a lower alkyl; X is O, S, NH; m and n are 0 to 4, Y1 is a halogen, cyano, a hydroxy, an amino, a lower alkyloxy, a lower alkylamino, a carboxy, a carbamoyl, a lower alkyl, etc., Y2 is hydrogen, an alkyl, cyano, -C(R3)=NR4 (wherein R3 and R4 are hydrogen, an amino, an alkyl, etc., or R3 and R4 may combine together with the nitrogen atom to form a 5- to 7-membered heterocyclic group), or a pharmaceutically acceptable salt thereof, or a non-toxic ester thereof, which has excellent antibacterial activity against Gram-positive bacteria, especially against MRSA and MRCNS.
(see formula 1) wherein R1 is a lower alkyl, a lower alkyl substituted by a hydroxy; R2 is a hydrogen, a lower alkyl; X is O, S, NH; m and n are 0 to 4, Y1 is a halogen, cyano, a hydroxy, an amino, a lower alkyloxy, a lower alkylamino, a carboxy, a carbamoyl, a lower alkyl, etc., Y2 is hydrogen, an alkyl, cyano, -C(R3)=NR4 (wherein R3 and R4 are hydrogen, an amino, an alkyl, etc., or R3 and R4 may combine together with the nitrogen atom to form a 5- to 7-membered heterocyclic group), or a pharmaceutically acceptable salt thereof, or a non-toxic ester thereof, which has excellent antibacterial activity against Gram-positive bacteria, especially against MRSA and MRCNS.
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2000341063 | 2000-11-08 | ||
| JP2000-341063 | 2000-11-08 | ||
| JP2001-126296 | 2001-04-24 | ||
| JP2001126296 | 2001-04-24 | ||
| JP2001273615 | 2001-09-10 | ||
| JP2001-273615 | 2001-09-10 | ||
| PCT/JP2001/009664 WO2002038564A1 (en) | 2000-11-08 | 2001-11-06 | NOVEL β-LACTAM COMPOUNDS AND PROECSS FOR PRODUCING THE SAME |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2427812A1 true CA2427812A1 (en) | 2003-05-02 |
| CA2427812C CA2427812C (en) | 2009-09-29 |
Family
ID=27345150
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002427812A Expired - Fee Related CA2427812C (en) | 2000-11-08 | 2001-11-06 | Novel .beta.-lactam compounds and process for producing the same |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US7163936B2 (en) |
| EP (1) | EP1340756B1 (en) |
| JP (1) | JP4213958B2 (en) |
| KR (1) | KR100814657B1 (en) |
| CN (1) | CN100379738C (en) |
| AT (1) | ATE375343T1 (en) |
| AU (1) | AU2002211006A1 (en) |
| CA (1) | CA2427812C (en) |
| CY (1) | CY1107837T1 (en) |
| DE (1) | DE60130916T2 (en) |
| DK (1) | DK1340756T3 (en) |
| ES (1) | ES2294035T3 (en) |
| PT (1) | PT1340756E (en) |
| TW (1) | TWI297689B (en) |
| WO (1) | WO2002038564A1 (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9149440B2 (en) * | 2003-09-02 | 2015-10-06 | University Of South Florida | Nanoparticles for drug-delivery |
| JP2006008641A (en) * | 2004-06-29 | 2006-01-12 | Sumitomo Pharmaceut Co Ltd | Method for producing optically active dihydropyrrole and tetrahydropyridine derivative |
| US20090018111A1 (en) * | 2004-10-08 | 2009-01-15 | Makoto Sunagawa | Novel Antimicrobial Medicament |
| WO2007142212A1 (en) * | 2006-06-08 | 2007-12-13 | Dainippon Sumitomo Pharma Co., Ltd. | Preparation composition |
| EP2229944A1 (en) | 2007-12-12 | 2010-09-22 | Dainippon Sumitomo Pharma Co., Ltd. | Preparation composition |
| TW200930722A (en) * | 2007-12-12 | 2009-07-16 | Dainippon Sumitomo Pharma Co | Stable crystal of β-lactam compound |
| WO2009093638A1 (en) * | 2008-01-25 | 2009-07-30 | Dainippon Sumitomo Pharma Co., Ltd. | PROCESS FOR PRODUCTION OF β-LACTAM COMPOUND |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5750686A (en) * | 1993-06-16 | 1998-05-12 | Sumitomo Pharmaceuticals Company, Limited | Carbapenem compounds and process for producing the same |
| JPH1077285A (en) * | 1996-09-04 | 1998-03-24 | Sumitomo Pharmaceut Co Ltd | Novel beta-lactam and its production |
| JP2000179834A (en) * | 1998-12-16 | 2000-06-27 | Rinnai Corp | Gas cock device |
-
2001
- 2001-11-06 CN CNB018217559A patent/CN100379738C/en not_active Expired - Fee Related
- 2001-11-06 US US10/416,334 patent/US7163936B2/en not_active Expired - Fee Related
- 2001-11-06 CA CA002427812A patent/CA2427812C/en not_active Expired - Fee Related
- 2001-11-06 WO PCT/JP2001/009664 patent/WO2002038564A1/en active IP Right Grant
- 2001-11-06 ES ES01979010T patent/ES2294035T3/en not_active Expired - Lifetime
- 2001-11-06 AT AT01979010T patent/ATE375343T1/en active
- 2001-11-06 DE DE60130916T patent/DE60130916T2/en not_active Expired - Lifetime
- 2001-11-06 KR KR1020037006034A patent/KR100814657B1/en not_active IP Right Cessation
- 2001-11-06 DK DK01979010T patent/DK1340756T3/en active
- 2001-11-06 JP JP2002541097A patent/JP4213958B2/en not_active Expired - Fee Related
- 2001-11-06 PT PT01979010T patent/PT1340756E/en unknown
- 2001-11-06 AU AU2002211006A patent/AU2002211006A1/en not_active Abandoned
- 2001-11-06 EP EP01979010A patent/EP1340756B1/en not_active Expired - Lifetime
- 2001-11-07 TW TW090127667A patent/TWI297689B/en not_active IP Right Cessation
-
2007
- 2007-12-18 CY CY20071101605T patent/CY1107837T1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP1340756A1 (en) | 2003-09-03 |
| EP1340756A4 (en) | 2004-08-11 |
| KR20030048104A (en) | 2003-06-18 |
| WO2002038564A1 (en) | 2002-05-16 |
| DE60130916D1 (en) | 2007-11-22 |
| CN100379738C (en) | 2008-04-09 |
| DE60130916T2 (en) | 2008-07-10 |
| KR100814657B1 (en) | 2008-03-18 |
| US20040102433A1 (en) | 2004-05-27 |
| CA2427812C (en) | 2009-09-29 |
| EP1340756B1 (en) | 2007-10-10 |
| TWI297689B (en) | 2008-06-11 |
| AU2002211006A1 (en) | 2002-05-21 |
| ES2294035T3 (en) | 2008-04-01 |
| JPWO2002038564A1 (en) | 2004-03-18 |
| JP4213958B2 (en) | 2009-01-28 |
| ATE375343T1 (en) | 2007-10-15 |
| PT1340756E (en) | 2008-01-15 |
| CY1107837T1 (en) | 2013-06-19 |
| US7163936B2 (en) | 2007-01-16 |
| CN1484645A (en) | 2004-03-24 |
| DK1340756T3 (en) | 2008-01-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed | ||
| MKLA | Lapsed |
Effective date: 20121106 |